DE3789464T2 - Lactonacrylat mit Carboxyl als Endgruppe. - Google Patents

Lactonacrylat mit Carboxyl als Endgruppe.

Info

Publication number: DE3789464T2
Authority: DE; Germany
Prior art keywords: acrylate; anhydride; acid; caprolactone; acrylates
Prior art date: 1986-02-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

DE3789464T

Other languages

German (de)

English (en)

Other versions

DE3789464D1 (de

Inventor

Joseph Victor Koleske

George Thomas Kwiatkowski

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Union Carbide Corp

Original Assignee

Union Carbide Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-02-20

Filing date

1987-02-20

Publication date

1994-07-28

1987-02-20 Application filed by Union Carbide Corp filed Critical Union Carbide Corp

1994-05-05 Application granted granted Critical

1994-05-05 Publication of DE3789464D1 publication Critical patent/DE3789464D1/de

1994-07-28 Publication of DE3789464T2 publication Critical patent/DE3789464T2/de

2007-02-21 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

-1 Lactone acrylate Chemical class 0.000 title claims abstract description 84
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title description 13
150000008064 anhydrides Chemical class 0.000 claims abstract description 43
239000000178 monomer Substances 0.000 claims abstract description 39
238000000576 coating method Methods 0.000 claims description 64
239000011248 coating agent Substances 0.000 claims description 49
238000006243 chemical reaction Methods 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 36
150000001252 acrylic acid derivatives Chemical class 0.000 claims description 24
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 16
125000002947 alkylene group Chemical group 0.000 claims description 14
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 13
UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 12
150000001735 carboxylic acids Chemical class 0.000 claims description 10
229920001577 copolymer Polymers 0.000 claims description 8
229920000642 polymer Polymers 0.000 claims description 8
150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 7
239000003054 catalyst Substances 0.000 claims description 6
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
239000008199 coating composition Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 4
238000007334 copolymerization reaction Methods 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
229920002554 vinyl polymer Polymers 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 3
229920000728 polyester Polymers 0.000 claims description 2
230000008569 process Effects 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000005855 radiation Effects 0.000 abstract description 18
239000000047 product Substances 0.000 description 75
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
239000004615 ingredient Substances 0.000 description 40
150000001875 compounds Chemical class 0.000 description 32
RZFODFPMOHAYIR-UHFFFAOYSA-N oxepan-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.O=C1CCCCCO1 RZFODFPMOHAYIR-UHFFFAOYSA-N 0.000 description 31
239000011521 glass Substances 0.000 description 25
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 21
239000000376 reactant Substances 0.000 description 20
QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 17
229910000831 Steel Inorganic materials 0.000 description 17
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 17
239000010959 steel Substances 0.000 description 17
150000002596 lactones Chemical class 0.000 description 16
239000002253 acid Substances 0.000 description 15
239000007795 chemical reaction product Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 11
230000004927 fusion Effects 0.000 description 11
239000002904 solvent Substances 0.000 description 11
125000004386 diacrylate group Chemical group 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
230000035484 reaction time Effects 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
150000003254 radicals Chemical class 0.000 description 9
239000000126 substance Substances 0.000 description 9
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 8
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
239000007888 film coating Substances 0.000 description 8
238000009501 film coating Methods 0.000 description 8
229920005862 polyol Polymers 0.000 description 8
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
238000001723 curing Methods 0.000 description 7
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical group OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 6
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical group OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
230000006872 improvement Effects 0.000 description 5
150000003077 polyols Chemical class 0.000 description 5
238000003847 radiation curing Methods 0.000 description 5
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
230000007423 decrease Effects 0.000 description 4
238000010894 electron beam technology Methods 0.000 description 4
239000003112 inhibitor Substances 0.000 description 4
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
229920001296 polysiloxane Polymers 0.000 description 4
239000004094 surface-active agent Substances 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
239000008103 glucose Substances 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
239000000976 ink Substances 0.000 description 3
230000007246 mechanism Effects 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
239000000049 pigment Substances 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
229920005992 thermoplastic resin Polymers 0.000 description 3
SZCWBURCISJFEZ-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) 3-hydroxy-2,2-dimethylpropanoate Chemical compound OCC(C)(C)COC(=O)C(C)(C)CO SZCWBURCISJFEZ-UHFFFAOYSA-N 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 2
QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 2
JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 description 2
MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 2
UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
VZTQQYMRXDUHDO-UHFFFAOYSA-N [2-hydroxy-3-[4-[2-[4-(2-hydroxy-3-prop-2-enoyloxypropoxy)phenyl]propan-2-yl]phenoxy]propyl] prop-2-enoate Chemical compound C=1C=C(OCC(O)COC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OCC(O)COC(=O)C=C)C=C1 VZTQQYMRXDUHDO-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
239000012965 benzophenone Substances 0.000 description 2
VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
230000008859 change Effects 0.000 description 2
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 2
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
239000002274 desiccant Substances 0.000 description 2
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239000000395 magnesium oxide Substances 0.000 description 1
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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239000003921 oil Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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229940112041 peripherally acting muscle relaxants other quaternary ammonium compound in atc Drugs 0.000 description 1
230000035699 permeability Effects 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000003504 photosensitizing agent Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
229920006122 polyamide resin Polymers 0.000 description 1
229920001610 polycaprolactone Polymers 0.000 description 1
239000004632 polycaprolactone Substances 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000005033 polyvinylidene chloride Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
ARJOQCYCJMAIFR-UHFFFAOYSA-N prop-2-enoyl prop-2-enoate Chemical compound C=CC(=O)OC(=O)C=C ARJOQCYCJMAIFR-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
150000004053 quinones Chemical class 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000007665 sagging Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
239000000565 sealant Substances 0.000 description 1
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125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
229920002803 thermoplastic polyurethane Polymers 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
229920006305 unsaturated polyester Polymers 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
229920006163 vinyl copolymer Polymers 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F20/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Macromonomer-Based Addition Polymer (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Paints Or Removers (AREA)
Polymerisation Methods In General (AREA)
Dental Preparations (AREA)
Sealing Material Composition (AREA)
Adhesives Or Adhesive Processes (AREA)

DE3789464T 1986-02-20 1987-02-20 Lactonacrylat mit Carboxyl als Endgruppe. Expired - Fee Related DE3789464T2 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/831,777 US4786749A (en)	1986-02-20	1986-02-20	Carboxyl-terminated lactone acrylates

Publications (2)

Publication Number	Publication Date
DE3789464D1 DE3789464D1 (de)	1994-05-05
DE3789464T2 true DE3789464T2 (de)	1994-07-28

Family

ID=25259845

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE3789464T Expired - Fee Related DE3789464T2 (de)	1986-02-20	1987-02-20	Lactonacrylat mit Carboxyl als Endgruppe.

Country Status (11)

Country	Link
US (1)	US4786749A (da)
EP (1)	EP0235704B1 (da)
JP (5)	JP2527952B2 (da)
KR (1)	KR870007961A (da)
AT (1)	ATE103583T1 (da)
AU (1)	AU6911087A (da)
BR (1)	BR8700817A (da)
CA (1)	CA1318326C (da)
DE (1)	DE3789464T2 (da)
DK (1)	DK86987A (da)
NO (1)	NO870685L (da)

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1986
- 1986-02-20 US US06/831,777 patent/US4786749A/en not_active Expired - Lifetime
1987
- 1987-02-19 CA CA000530088A patent/CA1318326C/en not_active Expired - Lifetime
- 1987-02-20 NO NO870685A patent/NO870685L/no unknown
- 1987-02-20 AT AT87102441T patent/ATE103583T1/de not_active IP Right Cessation
- 1987-02-20 AU AU69110/87A patent/AU6911087A/en not_active Abandoned
- 1987-02-20 KR KR870001421A patent/KR870007961A/ko not_active Withdrawn
- 1987-02-20 EP EP87102441A patent/EP0235704B1/en not_active Expired - Lifetime
- 1987-02-20 DE DE3789464T patent/DE3789464T2/de not_active Expired - Fee Related
- 1987-02-20 BR BR8700817A patent/BR8700817A/pt unknown
- 1987-02-20 JP JP62036003A patent/JP2527952B2/ja not_active Expired - Lifetime
- 1987-02-20 DK DK086987A patent/DK86987A/da unknown
1994
- 1994-10-12 JP JP6271810A patent/JP2811542B2/ja not_active Expired - Lifetime
- 1994-10-12 JP JP6271811A patent/JP2617429B2/ja not_active Expired - Lifetime
1996
- 1996-08-06 JP JP8221892A patent/JP2893656B2/ja not_active Expired - Lifetime
1998
- 1998-01-30 JP JP10032393A patent/JP2954917B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
JP2811542B2 (ja)	1998-10-15
JP2527952B2 (ja)	1996-08-28
JPH07258350A (ja)	1995-10-09
JPH09118724A (ja)	1997-05-06
ATE103583T1 (de)	1994-04-15
CA1318326C (en)	1993-05-25
JPH07258162A (ja)	1995-10-09
JP2893656B2 (ja)	1999-05-24
JP2617429B2 (ja)	1997-06-04
NO870685D0 (no)	1987-02-20
JPS62265249A (ja)	1987-11-18
US4786749A (en)	1988-11-22
KR870007961A (ko)	1987-09-23
JPH10310723A (ja)	1998-11-24
EP0235704B1 (en)	1994-03-30
DK86987A (da)	1987-08-21
JP2954917B2 (ja)	1999-09-27
DK86987D0 (da)	1987-02-20
EP0235704A3 (en)	1989-05-17
NO870685L (no)	1987-08-21
DE3789464D1 (de)	1994-05-05
EP0235704A2 (en)	1987-09-09
AU6911087A (en)	1987-08-27
BR8700817A (pt)	1987-12-15

Legal Events

Date	Code	Title	Description
1995-04-27	8364	No opposition during term of opposition
2004-12-09	8339	Ceased/non-payment of the annual fee

Publication	Publication Date	Title
DE1964547C3 (de)	1982-02-11	Verfahren zur Herstellung eines durch Strahlung härtbaren Überzugsmaterials
EP0235704B1 (en)	1994-03-30	Carboxyl-terminated lactone acrylates
EP0038300B1 (de)	1986-01-22	Polymerisierbare Zusammensetzung und (Meth)acrylsäureester
DE69026854T2 (de)	1996-10-31	Durch Strahlung härtbare Acrylatpolyester
DE2512642C3 (de)	1978-07-13	Durch aktinische Strahlung härtbare Masse
WO1998028345A1 (de)	1998-07-02	Verfahren zum herstellen von durch strahlung vernetzbaren polymeren acryl- oder methacrylsäureestern
DE2052961C3 (de)	1980-10-16	Mischpolymerisierbare Massen und Verfahren zu ihrer Herstellung
DE2651507B2 (de)	1980-10-16	Verwendung von Triacrylaten von oxäthyliertem Trimethylolpropan mit einem Oxäthylierungsgrad von 23 bis 4 als Verdünnungsmittel in strahlenhärtbaren Zusammensetzungen
WO2000008108A1 (de)	2000-02-17	Mit energiereicher strahlung und/oder thermisch härtbare bindemittel
DE69504355T2 (de)	1999-04-01	Strahlungshärtbare zusammensetzungen aus polyester und vinylether mit reaktivverdünner
DE69715197T2 (de)	2003-04-30	Photopolymerisierbare polyesterzusammensetzung und verfahren zu ihrer herstellung
DE60116858T2 (de)	2006-08-10	Zusammensetzung
AT392283B (de)	1991-02-25	Massen aus ungesaettigten polyestern oder polyesteramiden mit endstaendigen polycycloalkenylgruppen und vinyl-reaktive weichmacher hiefuer
DE2428491C3 (de)	1978-06-15	Flüssige ungesättigte Harzmasse
DE69610570T2 (de)	2001-02-08	Strahlungshärtbare Polymere und Verfahren zu ihrer Herstellung
DE69500640T2 (de)	1998-01-08	Michael-Additionsprodukte aus N-Vinylformamid und Ester aus Acryl und Methacrylsäure
DE2038659B2 (de)	1976-03-11	Durch ionisierende strahlung haertbare anstrichmittel sowie deren verwendung
EP0871678B1 (de)	2003-07-09	Polyfunktionell reaktive polymere stoffe
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DE19956779A1 (de)	2001-05-31	Vinylester mit hoher Vernetzungsdichte Verfahren zu ihrer Herstellung und Verwendung
DE2325179C2 (de)	1984-03-01	Mittels UV-Licht härtbare Form- und Überzugsmassen und Verfahren zu deren Herstellung
JP2893193B2 (ja)	1999-05-17	光硬化性樹脂組成物
DE2450621A1 (de)	1975-04-30	Organische, polymere verbindungen mit semi-telechelatartiger, olefinischer unsaettigung
DE19602071A1 (de)	1996-06-13	Strahlungshärtbare Massen, enthaltend Aminoalkenylether